Propanoic acid, 2,2-dimethyl-, cyanophenylmethyl ester

Base Information

• Chemical Name: Propanoic acid, 2,2-dimethyl-, cyanophenylmethyl ester
• CAS No.: 120345-61-1
• Molecular Formula: C13H15NO2
• Molecular Weight: 217.268
• Mol file: 120345-61-1.mol

Synonyms:

Chemical Property of Propanoic acid, 2,2-dimethyl-, cyanophenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Propanoic acid, 2,2-dimethyl-, cyanophenylmethyl ester

There total 4 articles about Propanoic acid, 2,2-dimethyl-, cyanophenylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

trimethylsilyl cyanide (7677-24-9) + 2,2-dimethylpropanoic anhydride (1538-75-6) + benzaldehyde (100-52-7) → O-2,2-dimethylbutyryl-2-hydroxy-2-phenylacetonitrile (120345-61-1)

Guidance literature:

trimethylsilyl cyanide; benzaldehyde; iron(III) chloride; In nitromethane; at 0 ℃; for 0.5h;

2,2-dimethylpropanoic anhydride; In nitromethane; at 60 ℃; for 2h;

DOI:10.1016/j.tetlet.2005.09.003

Reference yield: 76.0%

(RS)-mandelonitrile (532-28-5,613-88-7) + pivaloyl chloride (3282-30-2) → O-2,2-dimethylbutyryl-2-hydroxy-2-phenylacetonitrile (120345-61-1)

Guidance literature:

With pyridine; propan-1-ol; dmap; In toluene; at 20 ℃; for 14h;

DOI:10.1002/1099-0690(200205)2002:9<1516::AID-EJOC1516>3.0.CO;2-C

Reference yield:

benzaldehyde (100-52-7) + pivaloyl cyanide (42867-40-3) → O-2,2-dimethylbutyryl-2-hydroxy-2-phenylacetonitrile (120345-61-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; {(1R,2R)-[(3,5-tBu₂-2-OH-C₆H₂)-(E)-CH=N]2-cyclohexane-TiO₃}2; In dichloromethane; at -40 ℃; for 5h;

DOI:10.1002/adsc.200600365

upstream raw materials:

(RS)-mandelonitrile

pivaloyl chloride

trimethylsilyl cyanide

2,2-dimethylpropanoic anhydride

Downstream raw materials:

3,3-dimethyl-2-phenylbutanenitrile

Refernces

• 1、 Lundgren, Stina,Wingstrand, Erica,Moberg, Christina. "Lewis acid-lewis base-catalysed enantioselective addition of α-ketonitriles to aldehydes". . p. 364 - 372. Retrieved 2008/02/07.
• 2、 Veum, Lars,Kuster, Marina,Telalovic, Selvedin,Hanefeld, Ulf,Maschmeyer, Thomas. "Enantioselective synthesis of protected cyanohydrins". . p. 1516 - 1522. Retrieved 2007/10/03.